(E)-N'-(4-Isopropyl-benzyl-idene)isonicotinohydrazide monohydrate.

In the title compound, C(16)H(17)N(3)O·H(2)O, the isonicotinohydrazide mol-ecule adopts an E conformation about the central C=N double bond. The dihedral angle between the pyridine and the benzene rings is 54.56 (15)°. In the crystal, mol-ecules are connected via N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For details and the biological activity of isoniazide, see: Bloom & Murray (1992 ▶); Loenhout-Rooyackers & Veen (1998 ▶); Hearn et al. (2009 ▶); Tripathi et al. (2011 ▶).

Experimental

Crystal data

C16H17N3O·H2O

M = 285.34

Orthorhombic,

a = 7.7503 (2) Å

b = 11.7894 (3) Å

c = 17.2820 (4) Å

V = 1579.08 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.65 mm−1

T = 296 K

0.89 × 0.19 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.594, T max = 0.920

6473 measured reflections

2939 independent reflections

2499 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.145

S = 1.04

2939 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009099/cv5248sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009099/cv5248Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009099/cv5248Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H17N3O·H2O	F(000) = 608
Mr = 285.34	Dx = 1.200 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1751 reflections
a = 7.7503 (2) Å	θ = 4.5–65.6°
b = 11.7894 (3) Å	µ = 0.65 mm−1
c = 17.2820 (4) Å	T = 296 K
V = 1579.08 (7) Å3	Block, colourless
Z = 4	0.89 × 0.19 × 0.13 mm

Bruker SMART APEXII CCD area-detector diffractometer	2939 independent reflections
Radiation source: fine-focus sealed tube	2499 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 71.8°, θmin = 4.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→8
Tmin = 0.594, Tmax = 0.920	k = −13→10
6473 measured reflections	l = −20→21

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0715P)2 + 0.3351P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.22 e Å−3
2939 reflections	Δρmin = −0.28 e Å−3
193 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0045 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881, 1072 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.8 (4)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	1.1044 (3)	−0.05606 (15)	0.18186 (11)	0.0761 (6)
N1	1.1036 (4)	0.1562 (2)	−0.06565 (14)	0.0839 (8)
H1N1	0.9718	0.1817	0.2093	0.101*
N2	1.0132 (3)	0.11714 (17)	0.22203 (11)	0.0573 (5)
N3	1.0056 (3)	0.08469 (18)	0.29864 (11)	0.0578 (5)
C1	1.1390 (4)	0.1925 (2)	0.06922 (16)	0.0666 (7)
H1A	1.1742	0.2420	0.1080	0.080*
C2	1.1526 (5)	0.2221 (3)	−0.00740 (18)	0.0785 (9)
H2A	1.1990	0.2927	−0.0192	0.094*
C3	1.0378 (5)	0.0560 (3)	−0.04701 (17)	0.0835 (9)
H3A	1.0012	0.0089	−0.0869	0.100*
C4	1.0204 (4)	0.0177 (2)	0.02743 (15)	0.0670 (7)
H4A	0.9750	−0.0538	0.0374	0.080*
C5	1.0715 (3)	0.0872 (2)	0.08717 (13)	0.0536 (5)
C6	1.0648 (3)	0.0424 (2)	0.16813 (14)	0.0555 (6)
C7	0.9297 (3)	0.1536 (2)	0.34324 (14)	0.0571 (6)
H7A	0.8811	0.2185	0.3217	0.069*
C8	0.9143 (3)	0.1369 (2)	0.42615 (13)	0.0515 (5)
C9	0.9887 (4)	0.0448 (2)	0.46475 (15)	0.0604 (6)
H9A	1.0450	−0.0113	0.4366	0.072*
C10	0.9792 (4)	0.0366 (2)	0.54362 (15)	0.0689 (7)
H10A	1.0299	−0.0253	0.5680	0.083*
C11	0.8961 (4)	0.1178 (2)	0.58831 (15)	0.0692 (7)
C12	0.8237 (4)	0.2085 (3)	0.54993 (16)	0.0699 (7)
H12A	0.7684	0.2649	0.5783	0.084*
C13	0.8312 (4)	0.2176 (2)	0.47065 (15)	0.0611 (6)
H13A	0.7793	0.2792	0.4465	0.073*
C14	0.8851 (9)	0.1105 (4)	0.67642 (19)	0.1318 (19)
H14A	0.7599	0.1151	0.6836	0.158*
C15	0.9192 (7)	−0.0015 (4)	0.7099 (2)	0.1196 (15)
H15A	0.8882	−0.0011	0.7637	0.179*
H15B	1.0396	−0.0190	0.7048	0.179*
H15C	0.8521	−0.0576	0.6832	0.179*
C16	0.9387 (9)	0.2120 (5)	0.7158 (2)	0.149 (2)
H16A	0.8925	0.2121	0.7674	0.223*
H16B	0.8968	0.2771	0.6883	0.223*
H16C	1.0624	0.2145	0.7181	0.223*
O1W	0.8651 (3)	0.32125 (15)	0.18150 (11)	0.0822 (7)
H1W1	0.7748	0.3209	0.1531	0.123*
H2W1	0.8803	0.3754	0.2127	0.123*

	U11	U22	U33	U12	U13	U23
O1	0.1132 (16)	0.0556 (10)	0.0594 (10)	0.0199 (10)	0.0095 (11)	0.0108 (9)
N1	0.114 (2)	0.0893 (18)	0.0484 (12)	0.0015 (16)	0.0134 (14)	0.0090 (12)
N2	0.0738 (13)	0.0546 (12)	0.0436 (10)	0.0047 (10)	0.0017 (9)	0.0057 (8)
N3	0.0726 (13)	0.0566 (12)	0.0443 (10)	0.0010 (10)	−0.0025 (9)	0.0063 (9)
C1	0.0849 (17)	0.0594 (15)	0.0555 (14)	−0.0062 (13)	0.0094 (13)	−0.0003 (12)
C2	0.107 (2)	0.0670 (18)	0.0617 (17)	−0.0041 (16)	0.0213 (16)	0.0106 (14)
C3	0.113 (3)	0.086 (2)	0.0525 (15)	−0.0043 (19)	−0.0001 (16)	−0.0066 (14)
C4	0.0819 (18)	0.0642 (16)	0.0547 (14)	−0.0060 (14)	0.0020 (13)	0.0000 (12)
C5	0.0623 (13)	0.0537 (13)	0.0448 (11)	0.0029 (11)	0.0079 (10)	0.0043 (10)
C6	0.0638 (13)	0.0541 (14)	0.0486 (12)	0.0022 (11)	0.0030 (11)	0.0030 (10)
C7	0.0697 (14)	0.0512 (13)	0.0504 (13)	0.0021 (12)	−0.0057 (11)	0.0055 (10)
C8	0.0559 (11)	0.0526 (13)	0.0462 (11)	0.0002 (10)	−0.0027 (10)	0.0009 (9)
C9	0.0750 (16)	0.0530 (13)	0.0531 (13)	0.0117 (12)	0.0005 (12)	0.0027 (10)
C10	0.0871 (19)	0.0657 (16)	0.0538 (14)	0.0139 (14)	−0.0047 (13)	0.0083 (12)
C11	0.0913 (19)	0.0708 (17)	0.0455 (13)	0.0007 (15)	0.0039 (13)	−0.0005 (12)
C12	0.0798 (18)	0.0674 (16)	0.0624 (16)	0.0095 (14)	0.0115 (13)	−0.0081 (14)
C13	0.0659 (15)	0.0567 (14)	0.0607 (14)	0.0118 (12)	−0.0004 (12)	0.0022 (11)
C14	0.238 (6)	0.108 (3)	0.0494 (18)	0.018 (4)	0.006 (3)	0.0001 (19)
C15	0.149 (4)	0.149 (4)	0.0615 (19)	−0.022 (3)	0.008 (2)	0.034 (2)
C16	0.204 (5)	0.180 (5)	0.062 (2)	−0.002 (5)	−0.027 (3)	−0.026 (3)
O1W	0.1251 (18)	0.0586 (11)	0.0628 (11)	0.0163 (11)	−0.0286 (12)	−0.0119 (9)

O1—C6	1.224 (3)	C9—C10	1.368 (3)
N1—C3	1.326 (4)	C9—H9A	0.9300
N1—C2	1.327 (4)	C10—C11	1.389 (4)
N2—C6	1.343 (3)	C10—H10A	0.9300
N2—N3	1.379 (3)	C11—C12	1.377 (4)
N2—H1N1	0.8550	C11—C14	1.528 (4)
N3—C7	1.266 (3)	C12—C13	1.376 (4)
C1—C2	1.373 (4)	C12—H12A	0.9300
C1—C5	1.383 (4)	C13—H13A	0.9300
C1—H1A	0.9300	C14—C16	1.438 (6)
C2—H2A	0.9300	C14—C15	1.465 (6)
C3—C4	1.370 (4)	C14—H14A	0.9800
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.376 (4)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.496 (3)	C16—H16A	0.9600
C7—C8	1.451 (3)	C16—H16B	0.9600
C7—H7A	0.9300	C16—H16C	0.9600
C8—C13	1.382 (3)	O1W—H1W1	0.8541
C8—C9	1.398 (3)	O1W—H2W1	0.8437
C3—N1—C2	116.6 (3)	C9—C10—C11	122.0 (3)
C6—N2—N3	119.78 (19)	C9—C10—H10A	119.0
C6—N2—H1N1	121.2	C11—C10—H10A	119.0
N3—N2—H1N1	118.5	C12—C11—C10	117.1 (2)
C7—N3—N2	115.2 (2)	C12—C11—C14	120.1 (3)
C2—C1—C5	118.3 (3)	C10—C11—C14	122.7 (3)
C2—C1—H1A	120.9	C13—C12—C11	121.5 (3)
C5—C1—H1A	120.9	C13—C12—H12A	119.2
N1—C2—C1	124.1 (3)	C11—C12—H12A	119.2
N1—C2—H2A	117.9	C12—C13—C8	121.4 (3)
C1—C2—H2A	117.9	C12—C13—H13A	119.3
N1—C3—C4	124.0 (3)	C8—C13—H13A	119.3
N1—C3—H3A	118.0	C16—C14—C15	120.7 (4)
C4—C3—H3A	118.0	C16—C14—C11	114.1 (4)
C3—C4—C5	118.7 (3)	C15—C14—C11	115.8 (3)
C3—C4—H4A	120.7	C16—C14—H14A	100.3
C5—C4—H4A	120.7	C15—C14—H14A	100.3
C4—C5—C1	118.4 (2)	C11—C14—H14A	100.3
C4—C5—C6	118.8 (2)	C14—C15—H15A	109.5
C1—C5—C6	122.6 (2)	C14—C15—H15B	109.5
O1—C6—N2	124.2 (2)	H15A—C15—H15B	109.5
O1—C6—C5	120.5 (2)	C14—C15—H15C	109.5
N2—C6—C5	115.3 (2)	H15A—C15—H15C	109.5
N3—C7—C8	123.5 (2)	H15B—C15—H15C	109.5
N3—C7—H7A	118.2	C14—C16—H16A	109.5
C8—C7—H7A	118.2	C14—C16—H16B	109.5
C13—C8—C9	117.4 (2)	H16A—C16—H16B	109.5
C13—C8—C7	119.6 (2)	C14—C16—H16C	109.5
C9—C8—C7	122.9 (2)	H16A—C16—H16C	109.5
C10—C9—C8	120.5 (2)	H16B—C16—H16C	109.5
C10—C9—H9A	119.7	H1W1—O1W—H2W1	119.0
C8—C9—H9A	119.7
C6—N2—N3—C7	−169.0 (3)	N3—C7—C8—C13	179.0 (3)
C3—N1—C2—C1	0.0 (5)	N3—C7—C8—C9	2.7 (4)
C5—C1—C2—N1	0.6 (5)	C13—C8—C9—C10	−0.3 (4)
C2—N1—C3—C4	−0.9 (5)	C7—C8—C9—C10	176.0 (3)
N1—C3—C4—C5	1.0 (5)	C8—C9—C10—C11	0.2 (5)
C3—C4—C5—C1	−0.3 (4)	C9—C10—C11—C12	−0.4 (5)
C3—C4—C5—C6	−175.6 (3)	C9—C10—C11—C14	−179.6 (4)
C2—C1—C5—C4	−0.4 (4)	C10—C11—C12—C13	0.8 (5)
C2—C1—C5—C6	174.7 (3)	C14—C11—C12—C13	−179.9 (4)
N3—N2—C6—O1	1.3 (4)	C11—C12—C13—C8	−1.1 (5)
N3—N2—C6—C5	−178.9 (2)	C9—C8—C13—C12	0.8 (4)
C4—C5—C6—O1	38.5 (4)	C7—C8—C13—C12	−175.7 (3)
C1—C5—C6—O1	−136.6 (3)	C12—C11—C14—C16	−50.3 (7)
C4—C5—C6—N2	−141.4 (3)	C10—C11—C14—C16	128.9 (5)
C1—C5—C6—N2	43.6 (4)	C12—C11—C14—C15	162.9 (4)
N2—N3—C7—C8	−177.5 (2)	C10—C11—C14—C15	−17.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N1···O1W	0.85	1.90	2.757 (3)	176
O1W—H1W1···N1i	0.85	2.03	2.861 (3)	164
O1W—H2W1···O1ii	0.84	2.00	2.779 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N1⋯O1W	0.85	1.90	2.757 (3)	176
O1W—H1W1⋯N1i	0.85	2.03	2.861 (3)	164
O1W—H2W1⋯O1ii	0.84	2.00	2.779 (3)	154

Symmetry codes: (i) ; (ii) .